


Drag

by trillingstar



Category: Oz (1997)
Genre: Community: 50kinkyways, Crossdressing, F/M, M/M
Language: English
Status: Completed
Published: 2010-04-27
Updated: 2010-04-27
Packaged: 2017-10-09 04:39:16
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 982
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/83138
Author URL: https://archiveofourown.org/users/trillingstar/pseuds/trillingstar
Summary: <blockquote class="userstuff">
              <p>Keller thinks about dressing up.</p>
            </blockquote>





	Drag

**Author's Note:**

> Written for prompt #2: crossdressing on [50kinkyways](http://community.livejournal.com/50kinkyways) &amp; for [Oz Porn Tuesdays](http://trillingstar.livejournal.com/182013.html).
> 
> Thank you to [Rustler](http://archiveofourown.org/users/rustler) for her last-minute conditional II progressive knowledge, and for pimping simplicity.  
> 

  
"No shit?" he asked O'Reily.

"No shit," O'Reily confirmed.

"Huh," Keller said.

They played another hand in silence. Keller let O'Reily win, relieved not to be called on it. He pushed his chair back from the table. "Later."

O'Reily nodded distractedly, already scouting the quad for another sucker.

Stretched out on his bunk, Keller kicked his feet up over the bar at the end. Tucking his arms back under his head, he thought about that little gem that O'Reily had imparted.

He tried to picture it: Toby in a dress. Not only a dress, but stockings and heels, barrettes in his hair and makeup on his face. Keller bet Toby had looked awful in whatever Vern chose, 'cause Vern didn't have any taste, and Toby wasn't gonna look like a woman no matter what you put him in.

That sure as fuck wasn't the point, anyway; Toby's humiliation was the point, and Keller was sure that Vern's twisted idea of dress-up humbled Toby like nothing else. Poor fucker had to sing, in front of the whole goddamn prison, cons and hacks both, and McManus wondered why everybody hated his shitty guts. Vern embarrassed the fuck outta Chris more than once but he never pulled anything like that.

'Course, most men looked ugly as hell in a dress. Women, though. Women looked good in suits, button-down shirts and ties falling between their breasts, their hair pulled back tight, maybe even a fedora to top it off. Must've been some secret woman thing, that they could dress like men and it made them more beautiful. Men dressing like women made him laugh, even the real pretty ones who obviously spent hours trying to get everything just right.

He remembered seeing pictures of Kitty wearing a suit once, for some of the catalogue modeling that she'd done, the button-down open at her throat, one hand on her hip and the jacket slung over her shoulder, plastic smile fixed firmly in place. Angie had worn a suit for about fifteen seconds at the beginning of one of her numbers, and the closest he ever saw Bonnie to a suit was a pair of pinstripes and a blazer that she wore whenever her boss's boss came into the office.

Not that she didn't look great, with her hair pulled into a bun, and she'd wear her glasses that day 'cause she thought they made her look professional. She had this pretty colored shirt she wore under the jacket, with a neckline that showed off the pale skin of her chest. The jacket was old, still had those puffy shoulder pads inside that made her look like a drill sergeant, fierce, like she was in charge. Made him fucking hard is what that outfit did, and he was in heaven, watching her get dressed, panties-knee highs-pants-sensible shoes. He kinda admired that about her, that she'd never get caught dead in anything with a heel (though there was that one pair she wore to bed occasionally, with the poof of tickly pink feathers on the toes). Was a nice change from some of Angie's flashy platform stilettos; he kept waiting for her to wobble right out of 'em, but she pranced around as if they were glued to her feet.

Next, Bonnie would put on some kinda girdle that he hated looking at, blandly beige and holding in her belly, one of the softest parts of her that he loved the most. She'd lean over to put on her bra, jiggling her full tits at him, smiling coyly before covering them up, like a striptease in reverse. Shirt, hair up, classy silver earrings that he gave her for a birthday, a little stud shaped like a rose. The best part was watching when she shrugged into the jacket, then sat back down at the vanity to spritz on perfume right before she kissed him goodbye.

She'd grab her coat and purse and wave a tube of lipstick at him, glaring playfully. If she put the lipstick on before the kiss, he'd have it smeared across her cheek and chin by the end of the kiss, and she'd be moaning into his ear while he walked his fingers up under her bra and curled them around her breasts.

She'd get him all hot and bothered and then pull away and say things like _Not now, Chris_, and _I can't be late for work_, and then she'd brush her hand over his dick and whisper, _Save that for me until later_. He would promise to wait, and then he'd shove his hand into his boxers as soon as he heard the front door close. The thought of saving his hard-on for her made him want to stroke himself even more, and he never was good at waiting, especially when it wasn't like she was gonna know the difference.

Yeah, there was something about a woman - his woman - in a man's clothes that settled heavy in his gut, made him warm all over, and he always felt like going cruising after he'd watched her leave, after he'd jacked off, the smell of her perfume lingering in the bedroom. He rarely got home in time to see Bonnie take the clothing off, but after a night out? That was okay. He'd see her again in the morning, back to her big soft self, curves and rolls, wisps of hair against her cheeks, lips open in a moue as she put on her mascara.

He thought maybe Toby's mouth would make the same shape in the mirror, his eyelashes lengthening under the brush of the wand. He'd like to see lipstick smeared across Toby's cheeks and chin, taste the waxiness on his skin, suck on Toby's tongue until he squirmed away to gasp in a breath. Wondered if Toby might do that for him. Probably not. Still worth the thought, and his dick agreed.  



End file.
